Water → HCID 70665029, compound

HRID 1403655Notes

Reaction equation

HRID 1403655 reaction equation
[CH:1]1([N:5]([CH3:27])[C:6]2[C:7]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[N:8][C:9]3[C:14]([N:15]=2)=[CH:13][C:12]([C:16]([O:18]C)=[O:17])=[CH:11][CH:10]=3)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].O>CO>[CH:1]1([N:5]([CH3:27])[C:6]2[C:7]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)=[N:8][C:9]3[C:14]([N:15]=2)=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][CH:10]=3)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70664913HCID 70664913, compound

Product 1

HCID 70665029HCID 70665029, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(cyclobutyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (70.0 mg, crude) in MeOH (15 mL) was added sodium hydroxide (18.0 mg, 0.45 mmol) and water (0.5 mL). The resulting solution was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in water (10 mL) and adjusted to pH 3 with hydrochloric acid (1N). The solids were collected by filtration to afford 3-(cyclobutyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a yellow solid (30 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (10 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-f020b707c2764a1d85e48c94dffd0d86
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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